It really depends on your feet, and probably how far you plan to walk in them.
I know lots of older women who regret that they wore heals too much when they were younger. Uncomfortable shoes worn all day at a place like WDW can do permanent damage to your feet. So whatever shoes you pick (especially for all day wear), comfort on your feet should be your top priority.
At WDW, what is your priority? Is it to look good, for a few hours, then retreat. Or is it to ride as many attractions as you can.
Lots of times, I dress up-ish for dinner. Lots of time we only wear our long pants at night. So if that's the case, then you can get away with more pretty shoes perhaps. (Though often after dinner we sometimes go back to Mk for another six hours!) it really depends how long you plan to be on your feet, and how much you want your footware to be a limitation on your endurance. Personally if I told my family we had to go back very early because my shoes were pinching my feet, they'd be unhappy with me. I have made the mistake of wearing flip flops too long and regretted it the next day. It's not just one day your feet have to feel good, it's every day of your trip. Otherwise you'll be stuck in your room while everyone else had fun, or using a wheelchair. Foot injuries at WDw are no fun. I've been to WDW a number of times where someone in the family has a sore foot/leg, and it is no fun. (then we tend to go commando, and have a saying, "It's not a
real trip unless we come home limping!" But we have days where we open MK at 9am then close it down at 3am!)
I've had good luck with sandals and even some fancy flip flops. the flats I've had don't usually have enough arch support for me. I had a pair of Crocs flats that were okay, but I could not wear them all day. I only wore them if it was raining. They are dark blue and don't look like crocs. They aren't perfectly stylish, but they would be fine with skinny jeans.
Also, with skinny jeans, remember you are going to be getting in and out of rides all day. Some would be fine, others..Well, I hate to think about climbing into Space Mtn wearing very skinny jeans. And if you are wearing skinny jeans, you do NOT want to go on WET rides like Kali or Splash. You also don't want to wear a white t-shirt - if you catch my drift. It is a family park after all! you get attention for your looks, but probably not the kind you want

!
Oh, I have seen folks rip their pants at WDW! Also not a pretty site!